The present invention provides methods for altering, modifying or enhancing the organoleptic properties (aroma or taste) of consumable materials such as foodstuffs, tobacco products, and perfumes, by adding to such articles quantities of one or more 2-alkylidene-cis-3-alkenals and/or 2-alkylidene-trans-3-alkenals or di-lower alkyl acetals thereof and it further relates to compositions adapted to alter the organoleptic properties of consumable materials.
U.S. patent No. 3,463,818 shows unsaturated aldehydes having various floral odors and processes for preparing such compounds. Japanese published application No. 72/43526 shows the synthesis of terpene derivatives having orange-like odors, and hexadienal derivatives are shown. Wiemann et al, Memoires Presentes Soc. Chem., 1966, 1760, describe nuclear magnetic residence studies on some conjugated dienals, and a number of these compounds, including 2-ethylidene-3-pentenal are shown. 2-Propenyl-2-pentenal is mentioned in Chem. Abstracts 35, 6238.
West German published application 1,951,883 is said in Chem. Abstracts 75, 5246 show preparation of dienals useful as perfumes. Tiffeneau et al., Comptes Rend. 204, 590 show the preparation of 2-alkylidene-3-butenal.
U.S. Pats. Nos. 3,272,873; 3,453,317; and 3,493,619 show processes for preparing unsaturated aldehydes or for treating such aldehydes. U.S. Pat. No. 3,520,936 shows production of an unsaturated aldehyde, and U.S. Pat. No. 3,542,878 shows an aldol condensation using a tin catalyst.
Odiger et al. Annalen 682 58 (1965); Corey et al, J. Am. Chem. Soc. 90, 6816; and Wittig et al., Chem. Ber. 94, 676 (1961) show "alkylidenation" reactions utilizing phosphorous compounds.